With regards to Flair's World Title History as verified by Pro Wrestling Illustrated and WWE here are his official reigns...
1) Dusty Rhodes April 1981 (loses to Harley Race June 1983)
2) Harley Race (Starrcade 83) Nov 1983 (loses to Kerry Von Erich at Texas Stadium May 1984)
3) Kerry Von Erich (Japan) May 1984 (Best Of 3 Falls Match) (officially loses to Dusty Rhodes July 1986 Great American Bash in a Steel Cage Match)
This is where things start to get murky. Flair often took extra bookings on his time off that were not sanctioned by the NWA. In his book I think he said he worked on 3 week on, 2 week off schedule or something similar. In his off time he would take bookings often outside the US, making regular appearances in various South American Countries and Japan. In Japan, wrestling is huge and the US wrestling magazines often covered anytime US wrestlers appeared there. No such coverage followed US wrestlers appearing in other countries. Outside of Japan (where Flair was careful not to be booked to lose a title match) Flair would pull a promotional trick where he would come into the area as a heel, lose the title to the local promotion's #1 Fan Fave in a Rocky-like moment, thus ensuring major interest and a sell out for a re match shortly after, at which point Flair would prevail, although the local talent was still elevated by splitting two matches, often long, 45-60 minute affairs, with "The Great American Wrestling Champion". Flair estimates that he is at least a 20 time if not a 25 time champion if these "Title Swaps" were included.
In 1984 Flair & Race were touring Asia and agreed to do one of these switches. Even though Race was a 7 Time champ, had just held the belt last year, and was still involved in the NWA, this was not sanctioned by the NWA. The "Singapore Title Swap" as it was dubbed was initially ignored by the NWA and Pro Wrestling Illustrated.
It also wasn't uncommon for WWE and NWA wrestlers to face each other back then, although typically one of the wrestlers was in his own territory (like WWE Champ Bob Backlund facing NWA Champ Ric Flair in Atlanta). These matches were usually booked to be evenly fought and in inconclusively in a draw or double DQ, since they occurred in the US and might be carried by Pro Wrestling Illustrated and it's sister magazines. In 1985 Flair wrestled a Title vs Title Match vs AWA Champ Rick Martel in Japan that was covered in the US (ended in a 60 minute draw). Jim Crockett started restricting Flair from appearing in these matches in 1986, Bruiser Brody's stabbing death a year later kept Flair and several top US wrestlers from making South America trips, although Flair continued to wrestled in Japan (with NWA approval)
4) Dusty Rhodes Aug 1986 (loses to Ron Garvin in Sept 1987)
5) Ron Garvin (Starrcade 87 - No DQ Cage Match) - Loses to Ricky Steamboat at SuperBrawl 89 PPV Feb 1989.
6) Ricky Steamboat (Music City Showdown PPV May 1989) (Loses to Sting at 1990 Great American Bash PPV June 1990)
7) Sting Jan 1990 (Meadowlands Arena Show) - In late 1988 The Crocketts sold out to Ted Turner, although the NWA name was still used through 1990. The original name of the popular Sat evening wrestling show on TBS had been World Championship Wrestling, that name was adapted to the entire company in 1991 - This reign is officially considered the first title reign referred to as "WCW Champion".
In Feb 1991 Flair appears to be pinned by Tatsumi Fujinami in a show at the Tokyo Dome in Japan, crowning Fujinami champ. It's ruled that because Fuji flipped Flair over the top rope in front of the official ref (who was hurt in the ensuing fracas and did not count the pin I believe) that the match was actually a DQ. In Japan Fuji was still billed as Champ, complete with a press conference where an angry Flair "Steals the belt" and heads back to the US. In the states it's promoted as DQ win by Flair, but either way it sets up a re match in the states in May 1991, won by Flair. Initially WCW and PWI do not recognize this as a title switch and Flair is still officially a 7 time champ.
Flair is stripped of the WCW Title in June 1990 when he did not accept WCW's Contract offer - This is part of the infamous feud between Jim Herd, a Turner Broadcasting Exec put in charge of WCW by Turner, and Flair - Herd had previously forced Flair to cut his hair and wear an earing, and at one point wanted to turn him into a Roman Gladiator character complete with a sword & shield. Flair balked at those ideas, and also balked at Herd's contact offer which included a substantial pay cut down to around $200,000 from near a million previously. Flair had given notice and promised to lose the title (a story was already in the works where he would put over Lex Luger) but a further financial disagreement, this one over several thousand dollars WCW owed Flair for deposit money he put down to guarantee the safety of the Gold Belt Big Gold Belt started appearing on WWE TV and the debut of "The Real World's Champion" started being promoted. Eventually WCW sued Flair and while they got the belt removed from WWE TV they paid him a large sum of money, some estimates have it at $25,000, some higher, in a settlement.
8) Royal Rumble 1992 Winner for Vacant WWE Title Jan 1992 (loses to Randy Savage at WrestleMania VIII April 1992)
9) Randy Savage - Sept 1992 (loses to Brett Hart in Oct 1992) - WWE was building a major feud between Flair & Ultimate Warrior (Savage had taken himself off the road, asking for time off and a reduced schedule), supposedly with a title switch planned at Survivor Series. Warrior injured Flair at a house show and he couldn't keep wrestling. He agreed to lose the title in the ring to crown a new champ but WWE chose Hart instead of Warrior, despite Warrior already feuding with Flair. Not surprisingly Warrior dropped off WWE TV at the same time Flair did, not returning until almost two months later when Flair finally returned from his injury hiatus (he had broken bones in his ear from being dropped on his head and couldn't maintain his balance) just so Flair and Scott Hall could punk him on TV (explaining his disappearance from storylines).
Flair leaves WWE in Feb 1993 after a European Tour (he had just toured in Germany as WWE champ a few month earlier), officially recognized as a 9 Time World Champion by PWI.
10) Barry Whyndam - NWA Title Great American Bash June 1993 - This one is confusing. The original grouping of independent promoters that made up much of the original NWA was trying to reconfigure themselves as the original NWA of The Jim Crockett era with WCW viewed as a completely separate company. For awhile WCW agreed to this and helped revive the NWA Titles as separate entities and promoted them as such on their TV programs (unlike before when the NWA Titles were essentially continued on with the WCW name, like when the WWF changed it's name to WWE). For whatever reason PWI gave World Title recognition to this new NWA brand and treated Flair's win over champion Barry Whyndam as title #10, as does WWE. Before long the uneasy partnership between the new NWA & WCW dissolved and since the NWA Title was worn by a wrestler (Flair) under contract to WCW it was re christened the WCW International Championship and treated with the same level of importance as the WCW Title (kind of like the World Title on SmackDown vs the WWE Title on RAW today).
Flair lost the International Title to Rick Rude in Sept 1993
11) Vader (Starrcade 93 - Win Or Retire Match) Loses to Hulk Hogan at Bash At The Beach July 1994
More controversy - In Feb 1994 Flair vs Steamboat at SuperBrawl 94 ends in a double pin (both men appearing to pin each other). WCW Commissioner (and former multi time AWA Champ) Nick Bockwinkle declares the match a draw but "Suspends" the title until he makes his decision, Flair is nerver officially stripped but asks Bockwinkle to leave the title "suspended" until he can beat Steamboat in the ring, which he does a few weeks later. Although Flair is briefly described as a 12 time champion, WCW quickly reverses course and by the time the April PPV comes Flair is billed as an 11 time Champion.
Another controversy....WCW decides to unify the International & WCW Titles before Hogan arrives, at the June 1994 Clash Of Champions Flair pins Sting to unify the titles, effectively ending the International Title. Some people feel this should have given Flair an added reign, WCW and PWI treated it as a continuation of reign #11.
12) Randy Savage - Starrcade 95 - Flair had to beat Sting & Luger in a Triangle Match immediately before facing Savage, meaning he essentially beats WCW's 3 biggest names other than Hogan in consecutive matches to win the title (Loses to Savage in Jan 1996 on live Monday Nitro)
13) Randy Savage (No DQ Cage Match) Feb 1996 SuperBrawl PPV. The title switch on Nitro was done just to grab ratings, showing that anything could happen on a star studded live Nitro vs the taped and replayed later RAW (WWE wasn't live back then). Shortly after losing Flair earned his PPV re match by pinning Hulk Hogan on Nitro (first loss for Hogan in two years in WCW). This match was also where the Miss Elizabeth heel change occurred as she is instrumental in the match ending and becomes a fixture as Flair's manager for several months (loses to Giant, AKA Big Show, on April 1996 Nitro)
Around this time the Monday Night Wars were in full swing, and WCW was winning more often than not even though the NWO storyline hadn't started. WCW wanted to diminish anything WWE related and that meant not acknowledging Flair's two WWE Title reigns any longer. Problem was they had been billing him as an 11, 12, and 13 time champ repeatedly on TV including those reigns. WCW decided to acknowledge the "Singapore Title Swap" and count the Tatsumi Fujinami controversy as title changes, allowing Flair to remain a 13 time champ without the benefit of the WWE title wins. Eric Bischoff makes disparaging comments about the WWE title wins not being worthy or legit on Nitro during commentary a few times to show that Flair is a 13 time champ WITHOUT WWE. Officially PWI isn't recognizing this revised view of title history, which in theory would make Flair a 15 time champ in reality by the Spring of 1996
Flair has had a title reign in either WCW or WWE every year from 1981-1996.
14) Hulk Hogan (NO DQ, NO Holds Barred, Cage Match) - March 1999 Uncensored PPV. This is the infamous double character switch in which they try to turn Hogan face and Flair heel at the same time and it fails badly as the crowd does not want to cheer for Hogan (they were in Louisville , KY, which is in "Flair Country", which didn't help). Flair still gets a huge face pop when he pins Hogan and wins. (Loses to DDP in Fatal Four Way Match on PPV in April 1999 match including Hogan & Sting)
15) Jeff Jarrett on Monday Nitro - May 2000
More controversy here....shortly after the title win, a WCW Thunder taping, Flair is injured (more ear problems). Rather than wait a week or two to see what happens WCW immediately runs an angle where Flair is stripped of the title and the belt awarded to Jarrett by Vince Russo, also holding a "Funeral" for Flair on Nitro, which ends with Kevin Nash beating Jarrett for the title, giving each of them a title reign.
Flair wasn't seriously injured this time and is back wrestling a week later. Instead of playing off the "unfairly stripped of title" angle WCW books Nash to "award the title to Flair" because in his words "You never lost it". All this does is set up a Nitro Main Event where Jarrett beats Flair and wins the title leading us to...
16) Awarded Title From Kevin Nash May 2000 - After awhile, with Russo gone, WCW only refers to Flair as a 15 time champ but it's unclear if they are counting the WWE Titles or still ignoring them and adding title switches via the "Singapore Title Swap" & Fujinami Tokyo Dome incidents. They do not appear to acknowledge Flair as losing title #15, won from Jarrett, until Jarrett beats him on Nitro. On the final Nitro broadcast WCW calls Flair a 15 time champion. Also during Nitro's final year there are times when Flair is referred to as a 14 time champ even though it's after his win vs Jarrett. It seems WCW at this point in 2000-01 cant decide how they want to count Flair's title lineage.
The official 16 reigns listed here are the ones confirmed with PWI and listed by WWE in their promotional materials (including T-Shirts for Flair). I believe that the decisssion to count his 15th Title win over Jarrett and "Awarded Title From Kevin Nash" as separate reigns is because if you count that as one uninterrupted reign until his loss vs Jarrett then you have to erase title wins from Jarett & Nash's bios (Granted Jarrett was champ for maybe two hours and Nash for one week, but there are other incidents where a champ has had a title for similar short time, in fact I think Sting, HHH, & Cena have title reigns that didn't even last an entire PPV or TV Broadcast). Giving Jarrett & Nash credit as champs mean separating Flair's May 2000 into two separate reigns.
If you follow the revised WCW Monday Night Wars title lineage than Flair is an 18 time champ. PWI and WWE haven't done that, mainly because Singapore and Tokyo Dome were not counted as title losses when they occurred. I can agree with that because I don't like the idea of the company arbitrarily adding or deleting title reigns years after the fact just to serve a storyline, those moments were not considered title losses or wins when they happened and I believe they shouldn't be now.
Likewise the "Title Swaps" Flair used to do with various promotions outside the US back in the 80s were not sanctioned by the NWA, therefore I don't think they should be counted as title losses and wins.
As far as Orton and Cena vs Flair.....Flair had multiple reigns that lasted well over a year , something lacking in Orton's resume (Cena has three long reigns comparable to Flair's 80s reigns). Since the business model in terms of house shows vs PPVs is so different now it's hard for any wrestler to have even a single run like most of Flair's 80s runs, and Flair wasn't the only guy who had long runs in those days. Terry Funk had a year long NWA reign, SuperStar Graham had a year long WWE Reign, Backlund had a 5 year reign, Hogan's first WWE Run lasted from 1983-1988. Randy Savage also had a year long reign during that time. I think today if a champ maintains the title 6 plus months that's about as good as 12 month run in the previous era.
A better comparison would be length of time as a Go To, #1 Guy. Flair pretty consistently was either the going away #1 guy or one of the two or three very top guys consistently from 1981-1996, an extremely long time to maintain that level of involvement consistently at the top of the card. Cena as the Top Guy has lasted a little less than a decade, though he may reach Flair's longevity before he is done. In that sense I mean Flair's longevity as #1 guy, which you could carry to 1999 given his popularity and additional title reign. Obviously Cena has a long way to go to match Flair's over all level of longevity, still being a major attraction even if not in the title picture, which lasted roughly 35 years from the late 70s until his 2008 retirement. Given Cena's age I doubt he'll last that long, but then again other than Hogan who else can you say did last a comparable amount of time at that level ??
Orton has had a nice career, but Cena clearly has been the bigger star. Cena has also had more "meaningful" reigns than Orton. Some people will argue that he is not as entertaining as Flair (I agree) or as talented in the ring (I agree) but at the same time Cena has lived & breathed pro wrestling non stop for a decade, he's put over numerous people despite his star status, and consistently delivers high quality matches in big show and events regardless of his opponent (all qualities associated with Flair). If Cena breaks the record I don't think it will diminish Flair's accomplishments, and while I think it will be a nice add on for his career I don't think it suddenly puts him over Flair & Hogan as the greatest stars of a generation. Fact is Hogan could have more reigns if he didn't take so many extended leaves and Flair could have gotten more if he wasn't screwed by backstage politics with Bischoff and Hogan in WCW. How many would Steve Austin have had if not for his neck injury that prematurely ended his career, or Rock if he didn't leave for Hollywood ?
We'll never have an answer for those questions but a few things are indisputable...Cena has been the Franchise for WWE for almost a decade, looks to stay in that role a few years longer, and that's the best run anyone not named Flair or Hogan have had in the US since 1980, and that is nothing to be ashamed of diminished even if you don't think Cena reaches Hogan levels or SuperStardom or matches Flair's popularity and entertainment value.
